OP is making broad statements, and you might even be right about your guy. But even if your founder is not super wealthy from the first exit, your current startup could go under and if that happens employees will be left with absolutely nothing. Him, on the other hand, will probably have a golden parachute to land with. Either way he will be now be a "serial entrepreneur" and will be able to utilize his VC friends to start the next thing in no time. He's going to be fine.

And there's no telling what he will do if your startup does actually end up being worth something. Transfer the IP to a new company and fire everyone? Introduce new share classes for investors and dilute everyone else to zero? Sell the employees (acquihire) to some horrible BigCorp™ and then retire to Hawaii? No shortage of stunts they could pull once real money is on the table.